Chemoenzymatic Late‐Stage Modifications Enable Downstream Click‐Mediated Fluorescent Tagging of Peptides

Author:

Colombano Alessandro1ORCID,Dalponte Luca12,Dall'Angelo Sergio1ORCID,Clemente Claudia1ORCID,Idress Mohannad123ORCID,Ghazal Ahmad12,Houssen Wael E.12ORCID

Affiliation:

1. Institute of Medical Sciences University of Aberdeen Ashgrove Road West Aberdeen AB25 2ZD UK

2. Department of Chemistry University of Aberdeen Aberdeen AB24 3UE UK

3. Abzena, Babraham Research Campus Cambridge UK

Abstract

AbstractAromatic prenyltransferases from cyanobactin biosynthetic pathways catalyse the chemoselective and regioselective intramolecular transfer of prenyl/geranyl groups from isoprene donors to an electron‐rich position in these macrocyclic and linear peptides. These enzymes often demonstrate relaxed substrate specificity and are considered useful biocatalysts for structural diversification of peptides. Herein, we assess the isoprene donor specificity of the N1‐tryptophan prenyltransferase AcyF from the anacyclamide A8P pathway using a library of 22 synthetic alkyl pyrophosphate analogues, of which many display reactive groups that are amenable to additional functionalization. We further used AcyF to introduce a reactive moiety into a tryptophan‐containing cyclic peptide and subsequently used click chemistry to fluorescently label the enzymatically modified peptide. This chemoenzymatic strategy allows late‐stage modification of peptides and is useful for many applications.

Funder

Engineering and Physical Sciences Research Council

Industrial Biotechnology Innovation Centre

Publisher

Wiley

Subject

General Chemistry,Catalysis

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